1. Field of the Invention
The present invention relates to compounds of the general formula I ##STR2## where R is hydrogen or an aliphatic, alkenyl, cycloaliphatic, araliphatic, aromatic or heteroaromatic radical, R.sup.1 is hydrogen, amino, hydroxyl or C.sub.1 -C.sub.3 -alkyl, R.sup.2 is hydrogen, unsubstituted or substituted alkyl, allyl, aralkyl or aryl or alkylamino or arylamino, X is hydrogen, chlorine, bromine, nitro, methyl, phenoxy, tolyloxy, dimethylphenoxy, chlorophenoxy or C.sub.1 -C.sub.8 -alkoxy, Y is hydrogen, chlorine or bromine, and Z is hydrogen, acetyl, carbamyl or cyano.
2. Description of the Prior Art:
R is, for example, C.sub.1 -C.sub.17 -alkyl which can furthermore be interrupted by oxygen and substituted by, for example, phenyl, methylphenyl, carboxyl, a carboxylic ester group or unsubstituted or substituted phenoxy, or R is hydroxycarbonylvinyl, alkoxycarbonylvinyl, cycloalkyl of 5 to 7 carbon atoms, phenyl which is unsubstituted or substituted by chlorine, bromine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, or pyridyl or thienyl.
Specific examples of radicals R are methyl, ethyl, n- and i-propyl, n- and i-butyl, n- and i-pentyl, n-hexyl, n-heptyl, 1-ethylpentyl, decyl, undecyl, dodecyl, C.sub.15 H.sub.31, C.sub.17 H.sub.35, H.sub.5 C.sub.2 O.sub.2 CC.sub.2 H.sub.4 --, H.sub.9 C.sub.4 O.sub.2 CC.sub.2 H.sub.4 --, ##STR3## H.sub.3 COC.sub.2 H.sub.4 O.sub.2 CC.sub.2 H.sub.4, H.sub.5 C.sub.2 OC.sub.2 H.sub.4 O.sub.2 CC.sub.2 H.sub.4, H.sub.9 C.sub.2 H.sub.4 O.sub.2 CC.sub.2 H.sub.4, 2-ethylhexyloxymethyl and -ethyl, hexyloxyethyl, isopropoxyethyl, phenyl, chlorophenyl, cyclohexyl and in particular phenoxymethyl and -ethyl and benzyloxymethyl.
Alkyl radicals R.sup.2 are in particular, of not more than 18 carbon atoms, and can be straight-chain or branched. Phenyl-C.sub.1 -C.sub.4 -alkyl and unsubstituted or substituted phenyl or phenylamino are also suitable.
Specific examples of radicals R.sup.2 are methyl, ethyl, n- and i-propyl, n- and i-butyl, n-pentyl, n-hexyl, n- and i-heptyl, n- and i-octyl, n-nonyl, n-decyl, n-undecyl, phenyl, m-tolyl, p-tolyl, phenylamino, 2-ethylhexyloxypropyl, hexyloxypropyl, hydroxyethoxyethyl and hydroxybutoxypropyl.
Examples of alkoxy radicals X are octyloxy, .beta.-ethylhexyloxy, hexyloxy, phenoxy, amyloxy, butoxy, i-butoxy, propoxy, i-propoxy, ethoxy and, preferably, methoxy.
To prepare the compounds of the formula I, a diazonium compound of an amine of the formula ##STR4## can be reacted with a coupling component of the formula ##STR5## In the Examples which follow, and illustrate the preparation, parts and percentages are by weight, unless stated otherwise.
Of particular importance are compounds of the formula Ia ##STR6## where R is C.sub.3 -C.sub.17 -alkyl, or is C.sub.1 - or C.sub.2 -alkyl which is substituted by C.sub.4 -C.sub.8 -alkoxy, phenoxy or benzyloxy, or is C.sub.1 -C.sub.4 alkyl which is substituted by C.sub.1 -C.sub.8 -alkoxycarbonyl which may or may not be interrupted by oxygen, and R.sup.2 is hydrogen, C.sub.1 -C.sub.6 -alkyl or allyl, and R.sup.2 is not hydrogen when R contains a phenyl ring. Preferably the sum of the carbon atoms of R and R.sup.2 together is from 4 to 13, in particular from 5 to 11.
If R.sup.2 is hydrogen, R should preferably not contain a phenyl ring.
The compounds of the formula I are yellow disperse dyes which have very good fastness properties and excellent color strength. Moreover, the tinctorial properties are generally satisfactory.
Dyes which contain hydroxyl groups in R or R.sup.2 are, as a rule, suitable for leather and nylon.
Some of the dyes are also useful for printing on cotton and cotton/polyester blends, for example by the method described in German Patent No. 1,811,796.
The stated .lambda..sub.max values for the dyes were determined in a solution comprising 9 parts of dimethylformamide and 1 part of glacial acetic acid.